The appearance of Steinbrenner and Martin on the ballot together is almost too good to be true considering how inexorably the two were linked from the time Steinbrenner bought the Yankees until Martin’s untimely death on Christmas in 1989. However, an even more intriguing pairing involves one of the men who will be voting on Steinbrenner’s candidacy.

Billy Martin and George Steinbrenner in happy times. The two men are reunited as the only deceased candidates on the Hall of Fame's new Expansion Era ballot.

In order to get the posthumous nod, Steinbrenner will need a vote from 75% of the16-member panel, which the Boss would be pleased to know includes long-time friend and White Sox owner Jerry Reinsdorf. Steinbrenner would probably also be greatly amused by the irony of Reinsdorf sitting in judgment over his legacy because before the two became friends they were professional enemies.

Kemp caused a war of words between Steinbrenner and Reinsdorf in 1983.

The Reinsdorf/Steinbrenner feud began in the 1982 offseason when the Yankees made an aggressive play for White Sox outfielder Steve Kemp. When the ink dried on Kemp’s new five year, $5.5 million contract with the Yankees, Reinsdorf decried Steinbrenner’s fiscal irresponsibility and derisively stated that the Yankee owner was collecting bad contracts.

In addition to his public criticism, Reinsdorf also took aim at Steinbrenner by signing free agent pitcher Floyd Bannister to a five year, $4.5 million contract. The Yankees were rumored to have great interest in Bannister, so when Reinsdorf and fellow White Sox co-owner Eddie Einhorn had the last laugh with the signing, the Boss was not amused. In response to the Bannister contract, Steinbrenner fired back, telling AP, “[Reinsdorf and Einhorn] are the Abbott and Costello of baseball…a couple of pumpkins who should get their thinking straight”.

As thanks for turning that offseason’s winter meetings in Hawaii into a battle ground, baseball commissioner Bowie Kuhn fined Reindorf and Einhorn $2,500, but doubled the penalty for Steinbenner. Not surprisingly, the Boss bristled at being fined twice the amount as his adversaries, stating to AP, “I’m sorry to see that Kuhn is bowing out by bearing down on the owners as usual, especially me”.

Steinbrenner would eventually see justice delayed during the 1983 season when Reinsdorf was fined another $5,000 by Kuhn for once again taking a swipe at the Yankees’ owner. While attending a party for the All Star Game, which was being played at the White Sox’ Comiskey Park, Reindorf, who had a little too much to drink, entertained the attendees by explaining how to tell when George Steinbrenner was lying. “When you see his lips move,” Reindorf informed the crowd, which included Kuhn.

The Boss had his buddy beat on World Series championships (7 to 1), but Reinsdorf evened the score with the Bulls’ six NBA titles. In 1985, Reinsdorf purchased the Bulls from an ownership group that included Steinbrenner.

Kuhn wouldn’t last as commissioner for much longer. In August 1983, he eventually resigned, washing his hands of Steinbrenner and Reinsdorf, but in his absence, the two battling owners formed a strong friendship that would last for over 25 years.

Of course, just because they were friends, didn’t mean they still didn’t enjoy taking a dig at each other. The two teams were still fond of sabotaging each other in trades (the Britt Burns deal being an excellent example), and on a personal level, Reinsdorf always enjoyed flaunting his success with the Chicago Bulls, not the least of which was because one of the men from whom he bought them was Steinbrenner.

Very few men have a greater insight into Steinbrenner’s contribution to the game of baseball than Reinsdorf. As both an enemy and a friend, he has seen the best and worst of him. It remains to be seen which side will win out when Reinsdorf weighs the balance, but either way, you can bet the Boss is keeping a close eye on his buddy from up above.